My first time was a number of first experiences my first semester of college with a guy on my floor. We started with mutual masturbation, after a week or so we moved on the fingering and handjobs, a couple weeks later we started doing oral. Towards the end of the semester I finally told him I wanted him to fuck me, a couple days later he had condoms. It was both of our first times so we had no idea what position would work best. We tried a few different positions, but finally settled on me sitting on his desk and him standing. We took it really slow, and it felt amazing after all that time doing other stuff with him. He made me cum, then he immediately came as well inside me with the condom.